Zifeng Qin, Wei Liu, Dan-Jie Wang
May 13, 2016
Citations
0
Influential Citations
25
Citations
Journal
The Journal of organic chemistry
Abstract
A phosphine-catalyzed (4 + 1) annulation reaction of o-hydroxyphenyl and o-aminophenyl ketones with ester-modified allylic carbonates has been developed, providing a facile and efficient method to synthesize functionalized 2,3-disubstituted dihydrobenzofurans and indolines. Under mild conditions and in the catalysis of PPh3 (20 mol %), the reactions of o-hydroxyphenyl or o-aminophenyl ketones readily furnish highly functionalized 3-hydroxy-2,3-disubstituted dihydrobenzofurans or 3-hydroxy-2,3-disubstituted indolines in 40-99% yields with generally high diastereoselectivity. To further expand the utility of this annulation reaction to the synthesis of functionalized benzofurans and indoles, the CuSO4-promoted chemical transformations of the annulation products have also been studied.